Kathy finally took anal. Of course, I had been waiting for this day, but I didn’t want to rush her; at the same time, I didn’t want to risk missing the chance in case something happened or she had a change of heart. I told her what I wanted on the way to her place, and she said she was up to it. After the usual sexual warm-ups and cunnilingus-fest, we were ready to go. I suggested that she use her vibrator when we got to that point, but I needed to make sure she was prepared so she’d have a positive first experience. I told her it wouldn’t be substantially different to her first time having sex, but like regular sex she’d quickly get the hang of it. She was less nervous than I might have expected.
I got her into doggy position and started where we left off last week, getting her ass ready for a visitor, whilst taking her from behind. This time I had the AstroGlide out instead of oil. In a matter of five or so minutes, I had managed to work three fingers into her tight ass, and I was ready to take the plunge. I confirmed that she was ready and told her to fire up her trusty vibrator before I got continued. I pulled out of her pussy, and she targeted the vibrator onto her clit. (I guess she’s been practising.) While she continued to pleasure herself, it was time for me to continue my journey.
I had relaxed her ass pretty well, but I didn’t want to spook her, so I took it extra slow. After some initial resistance, I could feel the head of my cock snap past her sphincters, so I paused for her to get used to it. She flinched for only a moment, I didn’t move for about a minute, and then I was ready to go in deeper. I rocked my hips with each gentle thrust getting deeper and deeper, it seemed about a millimeter each one.
She started to indicate that it was becoming painful, so I stopped for a few moments and asked her how she was feeling. She said that it hurt a bit, but it still felt good. She said it was OK for me to continue. I could feel her tensing her body (and her ass) as I went in deeper. When I finally got all the way in, I paused again and told her that I was in as deep as I could go. I think she was relieved, but she said it was still uncomfortable. At that point I pulled out, applied more lube, and put my cock back into her ass. This time, I fucked her slowly, taking normal strokes, in and out. I found a nice rhythm, and she started to settle down and relax somewhat.
Next thing I knew, I thought she was going to hyperventilate. She started panting and moaning LOUDLY. As long as I’ve been with her, she’s been quite in bed, but not this time: she repeated over and over, “don’t stop, don’t stop, don’t stop…”After a short while, she came hard, and she was definitely out of breath. I could feel the shift in her energy. Now she was really relaxed. I guess she was over the hump.
She put aside her vibrator, and I started to take nice long strokes and fully enjoy the experience. When I asked if it was still uncomfortable, she said no, that it felt good. Then I came. I had a nice cum, too, and I collapsed on her with my cock still in her ass.
“That was great,” I told her. She said it was amazing, that she couldn’t have imagined having such as strong orgasm. “So, I guess you’ll be OK if we do this again?” I asked. She answered, “Definitely.”
We took a quick shower together, and headed back to work. She seemed giddy the whole trip.